Discover Your Perfect Jessamine County Vacation Homes

Why Choose Rent By Owner for your Jessamine County Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Jessamine County

When should you plan your Vacation Rentals stay?

Timing your visit to this charming area can enhance your experience, as choosing the best season allows you to enjoy its unique attractions and peaceful surroundings at their peak.

Peak Season Highlights

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Spring (March to May)

During spring, the area comes alive with blooming flora and pleasant weather, making it an ideal time to enjoy outdoor activities.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
autumn
Fall (September to November)

The fall season offers vibrant foliage and cooler temperatures, perfect for exploring scenic views and outdoor adventures.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Off-Season Highlights

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Summer (June to August)

In summer, the region experiences warmer days that are great for daytime exploration, though some may find it less crowded.

Average Temperature Daytime: 85°F to 90°F - Nighttime: 65°F to 70°F
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Winter (December to February)

Winter brings colder temperatures and quieter surroundings, providing a peaceful atmosphere perfect for cozy stays.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°F

Weekly Weather Forecast for Jessamine County

How to Book Your Jessamine County Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Jessamine County

More Top-Rated Vacation Rentals in Jessamine County Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor dining areas perfect for relaxing meals amid scenic views.
  • Take advantage of spacious yards or gardens ideal for outdoor activities or gatherings.
  • Relax in private patios or decks that offer a peaceful retreat after exploring the area.
  • Make use of outdoor fire pits for cozy evenings under the stars.
  • Benefit from bicycle or walking paths to explore the natural beauty surrounding your stay.
  • Utilize outdoor swimming pools available in some rentals to cool off during warmer months.
  • Discover well-maintained lawns or green spaces suitable for picnics and leisure activities.

Top Attractions Around Jessamine County

What attractions are nearby?

During your stay, you can explore local parks, enjoy outdoor recreational activities, and discover charming historic sites just moments from your vacation rentals here in Jessamine County, Kentucky.

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Family Activities

  • Carroll Road Park: Enjoy outdoor adventures with your family at this scenic park offering playgrounds, walking trails, and picnic areas perfect for a relaxing day in the region.
  • Bluegrass Railroad Museum: Explore railroad history through engaging train rides and exhibits that captivate children and adults alike here in the local area.
  • Wilmore Waterpark: Beat the summer heat by visiting this popular waterpark featuring slides and lazy rivers, providing hours of fun for the entire family.
  • Jessamine County Nature Center: Discover the region’s natural beauty through educational exhibits, wildlife viewing, and nature trails ideal for family outings in the area.
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Adult Activities

  • Exploring local wineries: You can enjoy tasting tours at the region’s distinguished wineries, discovering unique Kentucky vintages in a relaxed setting.
  • Visiting historic sites: Delve into the area's rich history by touring renowned landmarks and museums that highlight its cultural heritage.
  • Participating in outdoor recreation: Take advantage of scenic parks and trails for activities like hiking and birdwatching amid the natural beauty here.
  • Enjoying local dining experiences: Sample Southern-inspired cuisine at charming eateries that showcase the region's culinary traditions.

Other Places to Stay in Jessamine County, KY

Chrisman Mill Vineyards
Chrisman Mill Vineyards Vacation Rentals
Connemara Golf Course
Connemara Golf Course Vacation Rentals
First Vineyard
First Vineyard Vacation Rentals
BlueGrass Renal Care
BlueGrass Renal Care Vacation Rentals
CHI Saint Joseph Health - Saint Joseph Jessamine
CHI Saint Joseph Health - Saint Joseph Jessamine Vacation Rentals
High Bridge
High Bridge Vacation Rentals
Asbury University
Asbury University Vacation Rentals
Wilmore
Wilmore Vacation Rentals
Jd Legends Bar & Grill
Jd Legends Bar & Grill Vacation Rentals
Nicholasville
Nicholasville Vacation Rentals
Camp Nelson Civil War Heritage Park
Camp Nelson Civil War Heritage Park Vacation Rentals
Wolf Run Wildlife Reserve
Wolf Run Wildlife Reserve Vacation Rentals
More Places to Stay Near Jessamine County

Jessamine County Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Visit During Off-Peak Seasons: Visiting during less busy times allows you to enjoy the area’s attractions and your vacation rental with more tranquility and better availability.
  • Explore Local Dining Options: Take advantage of nearby eateries to experience authentic regional cuisine that complements your stay in this charming destination.
  • Take Advantage of Nearby Outdoor Activities: Make the most of the region’s scenic parks and outdoor spaces for activities like hiking or picnicking that enhance your overall experience.
  • Prioritize Comfortable Accommodation Choices: Choose a well-reviewed vacation rental that offers amenities suited to your needs, ensuring a relaxing and enjoyable stay here.

Transportation Options

  • Jessamine County Transit System: This local transit service provides convenient, cost-effective transportation around the area and connects you to key destinations within the region.
  • Rental Cars at Lexington Blue Grass Airport: You can easily rent a vehicle upon arrival at the nearby airport, offering flexibility to explore here at your own pace.
  • Taxi Services: Reliable taxi companies operate throughout the region, providing quick access to vacation rentals and popular local spots.
  • Rideshare Options: Uber and Lyft are readily available in this destination, giving you a modern and convenient way to travel without needing a personal vehicle.

Local Customs Options

  • Kentucky Hospitality Tradition: You'll find that locals here take pride in their warm and inviting spirit, often welcoming visitors with genuine friendliness and a sense of community.
  • The region’s deep-rooted bourbon tradition influences many local customs, reflected in the appreciation for quality spirits and the celebrations centered around this iconic Kentucky craft.
  • As part of the area's rich equestrian culture, you'll notice respectful practices during horse events and an emphasis on supporting local breeders and trainers.
  • Embracing Southern culinary traditions, it’s common to enjoy hearty, locally-inspired dishes that highlight the area's farm-fresh ingredients and family recipes.

Frequently Asked Questions About Jessamine County?

1. What are the top vacation rentals in Jessamine County?

There are a lot of options in Jessamine County. If you plan on staying in the Jessamine County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Jessamine County:

2. Which vacation homes in Jessamine County are best for families?

If you are looking for a family-friendly vacation home in Jessamine County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Jessamine County:

3. How many Rentbyowner vacation rentals are available in Jessamine County?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 34 in the Jessamine County area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Jessamine County. 

4. What is the cancellation policy for vacation rentals in Jessamine County, Kentucky?

The cancellation policies vary by property. You should review the specific listing details or contact the property owner directly to understand the terms and any applicable fees before confirming your reservation.

5. How do I know if a vacation rental in Jessamine County has the amenities I need?

Each listing provides a detailed description of its amenities. To ensure the property meets your needs, carefully read the listing details or reach out to the owner with any questions before booking.

6. Are there any additional fees I should be aware of when booking a vacation rental in Jessamine County?

Additional fees such as cleaning, service charges, or security deposits are often included in the listing details. Confirm these costs with the owner during the booking process to avoid surprises.

7. What is the check-in and check-out process for vacation rentals in this area?

Check-in and check-out procedures are specified in each listing. Contact the property owner if you have any special requests or need clarification on the process before your arrival.

8. Is it possible to modify or cancel my reservation in Jessamine County once booked?

Reservation modifications and cancellations depend on the property's policy. Review the listing's cancellation policy or contact the owner directly to discuss any changes you need to make.